Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction

被引：258

作者：

Matsui, K ^{[1
]}

Takizawa, S ^{[1
]}

Sasai, H ^{[1
]}

机构：

[1] Osaka Univ, ISIR, Ibaraki, Osaka 5670047, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 11期

关键词：

D O I：

10.1021/ja0500254

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid-base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol. Copyright © 2005 American Chemical Society.

引用

页码：3680 / 3681

页数：2

共 48 条

[1] The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions
Aggarwal, VK
Castro, AMM
Mereu, A
Adams, H
[J]. TETRAHEDRON LETTERS, 2002, 43 (08) : 1577 - 1581
[2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[3] Catalyst analogue: A concept for constructing multicomponent asymmetric catalysts (MAC) by using a polymer support
Arai, T
Sekiguti, T
Otsuki, K
Takizawa, S
Sasai, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (19) : 2144 - 2147
[4] A dendrimer-supported heterobimetallic asymmetric catalyst
Arai, T
Sekiguti, T
Iizuka, Y
Takizawa, S
Sakamoto, S
Yamaguchi, K
Sasai, H
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (19) : 2083 - 2087
[5] RELATIONSHIPS BETWEEN THE THERMODYNAMICS OF PROTONATION IN THE GAS AND AQUEOUS PHASE FOR 2-SUBSTITUTED, 3-SUBSTITUTED, AND 4-SUBSTITUTED PYRIDINES
AUE, DH
WEBB, HM
DAVIDSON, WR
TOURE, P
HOPKINS, HP
MOULIK, SP
JAHAGIRDAR, DV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) : 1770 - 1780
[6] A new protocol for the Baylis-Hillman reaction: the reaction of iminium salts prepared in situ with methyl acrylate
Azizi, N
Saidi, MR
[J]. TETRAHEDRON LETTERS, 2002, 43 (24) : 4305 - 4308
[7] Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction
Balan, D
Adolfsson, H
[J]. TETRAHEDRON LETTERS, 2003, 44 (12) : 2521 - 2524
[8] Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives
Balan, D
Adolfsson, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) : 2329 - 2334
[9] Recent advances in the Baylis-Hillman reaction and applications
Basavaiah, D
Rao, AJ
Satyanarayana, T
[J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
[10] PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES
BERTENSHAW, S
KAHN, M
[J]. TETRAHEDRON LETTERS, 1989, 30 (21) : 2731 - 2732

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